Throughout the early history of the New Windsor area, the Town shifted frequently between counties. The New Windsor area was incorporated into Charles County in 1658, but in 1694 the area was transferred to Prince George’s County. In June of 1748, the area then shifted to Frederick County. Not until 1837, when Carroll County was created, was it incorporated into Carroll.
The Town of New Windsor was laid out and surveyed into 28 lots in 1797 by Isaac Atlee who hailed from Lancaster, Pa. He hoped to capitalize on traffic coming to and from Winchester, Va. and Philadelphia on a spur that fed the old Monocacy Road, a wagon trail situated some miles north of town. The area also enjoyed traffic on the Buffalo Road, connecting Annapolis to parts north. This colonial thoroughfare was named after a buffalo trail that predated the arrival of settlers and is today’s High Street. A novice real estate speculator, Atlee saw the crossroads that is now Main and High Streets as a natural location for a town.
One of the most notable structures in town is the 10,000 square foot, 42 room Dielman Inn at High and Main Streets. It was a popular gathering place for vacationers from the 1870s through its closing in 1927. In its prime, the inn became a regional cultural magnet, and this also served to attract visitors. The proprietor was Louis William Dielman, a former professor of music at Calvert College in town. He delighted in sponsoring after-dinner concerts, musicales, lectures, skits and tableaux featuring guests who hailed from as far away as New York. For years, a regular visitor was retired Brigadier General Marion P. Maus, a Congressional Medal of Honor winner who was credited with the capture of Geronimo in 1886.
The town is proud of its unique architecture. Elegant, stately homes sit at the top of Church Street, originally called Quality Hill. There you will find houses constructed in the Colonial Revival, Classical Revival, Queen Anne, and Bungalow styles.
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